Hydrochloric Acid → HCID 21192589, compound

HRID 1067954Notes

Reaction equation

HRID 1067954 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([I:14])=[CH:11][CH:12]=3)[C:7](=[O:15])[C:6]([C:16]([O:18]CC)=O)=[CH:5]2)[CH2:3][CH2:2]1.[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.ClCCl.Cl>CO>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][C:16]([C:6]2[C:7](=[O:15])[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=3)[N:4]([CH:1]3[CH2:2][CH2:3]3)[CH:5]=2)=[O:18])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 660364-ChlorobenzylamineHCID 21192588HCID 21192588, compound

Product 1

HCID 21192589HCID 21192589, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

To a flask containing ethyl 1-cyclopropyl-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate from Preparation No. 19 (0.19 g) is added p-chlorobenzylamine (1.0 mL). The reaction is tightly capped and heated to 180° C. for 1 hour. The reaction is cooled to room temperature and partioned between dichloromethane containing methanol and dilute hydrochloric acid. The aqueous layer is extracted with dichloromethane and the combined organic layers are washed with brine, dried and concentarted under reduced pressure. The residue is adsorbed onto silica and chromatographed on silica eluting with 2% to 6% methanol in dichloromethane. The product containing fractions are evaporated to give 0.10 g of the title compound as a tan solid.

Workup

  1. customfrom Preparation No
  2. customThe reaction is tightly capped
  3. temperatureThe reaction is cooled to room temperature
  4. extractionThe aqueous layer is extracted with dichloromethane
  5. washthe combined organic layers are washed with brine
  6. customdried
  7. customchromatographed on silica eluting with 2% to 6% methanol in dichloromethane
  8. additionThe product containing fractions
  9. customare evaporated

Sources & evidence

ORD record
ord-481d449fb8a44f689113986e34bac7e4
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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